1-(2-Chloro-7-fluoroquinolin-3-yl)ethanol → HCID 24276110, compound

HRID 75358Notes

Reaction equation

HRID 75358 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]([OH:14])[CH3:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][CH:8]=2)[N:3]=1>O=[Mn]=O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 242760771-(2-Chloro-7-fluoroquinolin-3-yl)ethanol

Product 1

HCID 24276110HCID 24276110, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

1-(2-Chloro-7-fluoroquinolin-3-yl)ethanol (7.7 g, 34 mmol), MnO2 (30 g, 10 eq) and Toluene (200 mL) were heated to reflux for 2 h. LC-MS showed completion of the reaction. Filtration followed with removal of solvent gave an off-white solid of 1-(2-chloro-7-fluoroquinolin-3-yl)ethanone (6.2 g, 81%). Mass Spectrum (ESI) m/e=224 (M+1).

Workup

  1. temperatureto reflux for 2 h
  2. customcompletion of the reaction
  3. filtrationFiltration
  4. customfollowed with removal of solvent

Sources & evidence

ORD record
ord-cb578d6717f84699b195834164fdd0f1
Source dataset
uspto-grants-2014_09
Patent number
US08835432B2

Reaction notes

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